DENNIS: Well, in that case… hello, my name is Dennis, and my phone number is 555-6969… But seriously, I’d like to suggest a minor change to your plan: instead of deciding that the next guy you date — and like — is going to be the one, how about deciding that if the next guy you date — and like — turns serious enough, then he’ll be the one?
If you’re so set on losing your virginity to the next guy you go out with, don’t you think you might become just a bit too eager and end up regretting your decision? You’ve waited 23 years. Why rush at this point? To answer the question, though: yes, I think you should tell him. But, definitely don’t tell him that the next guy is going to be the one. Because then you’re just opening yourself up to get screwed over (pun intended). Just tell him that you’re ready to lose your virginity… to the right guy. Good luck!
ANDREW: You probably don’t want to tell him on the first date but, when it’s time, it might make for a better and more intimate experience if you do tell him. Whether or not it will “freak him out” there’s really no way of knowing… UNLESS YOU SLEEP WITH ANOTHER VIRGIN! Do it! Grab that nice shy guy you only think of a as a friend and get naked with him! Let’s be honest, your first time will more than likely be a disappointment anyway, so your best shot at uninhibited exciting sex is gonna be with a guy in the same virginal boat as you. It probably won’t be good sex but I bet it’ll be a fun and shame free. That makes for a pretty good first time.
DAVE: First off… congratulations. The only thing I respect more than a 23-year old virgin is a 24-year old virgin. (Granted, it gets creepy once you get into your 30’s). The fact that you have been able to maintain your virtue for so long only punctuates how important it must really be for you to share it with just the right person. You are in a situation now where you need to RAISE the bar, not lower it. Seek out a mate who shares your values — someone who is worthy of you. Think how wonderful it would be if he was a virgin too, and how you could do things at your own pace as you set out on your committed relationship. Plus… no fear of social diseases!
You do not HAVE TO wait until you get married, but at the very least wait until you fall in love with someone that you’d like to marry, and who feels the same about you. In that way, sex doesn’t become that big “be all, end all” in the relationship; it takes its rightful place as just one of the many wonderful shared experiences in a long term relationship.
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